(1R,9aS)-octahydro-1H-quinolizin-1-ol | 907188-96-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹嗪类
• 英文名称: (1R,9aS)-octahydro-1H-quinolizin-1-ol
• 英文别名: trans-1-Hydroxychinolizidin；cis-1-Hydroxychinolizidin；(1R,9aS)-Octahydro-2H-quinolizin-1-ol；(1R,9aS)-2,3,4,6,7,8,9,9a-octahydro-1H-quinolizin-1-ol
• CAS: 907188-96-9
• 化学式: C₉H₁₇NO
• 分子量: 155.24
• InChiKey: MTVNMVKUNMOINI-DTWKUNHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1R,9aS)-octahydro-1H-quinolizin-1-ol 在 sodium azide 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 18.5h， 生成 (1S,9aS)-1-azido-2,3,4,6,7,8,9,9a-octahydro-1H-quinolizine
  参考文献：
  名称：

  A concise synthesis of (±) and a total synthesis of (+)-epiquinamide

  摘要：

  A total synthesis of the quinolizidine alkaloid (+)-epiquinamide 1 has been achieved starting from (-)-pipecolinic acid 3. The key step is the highly diastereoselective addition of a TBDMS-protected propargyl alcohol to a chiral aldehyde derived from 3 to give erythro alkynol 19, which is then easily transformed into the desired bicyclic skeleton. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.05.092
• 作为产物：
  描述：

  (S)-2-甲酰基-1-哌啶甲酸叔丁酯 在 palladium on activated charcoal sodium hydroxide 、 正丁基锂 、 四丁基氟化铵 、 氢气 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 反应 34.42h， 生成 (1R,9aS)-octahydro-1H-quinolizin-1-ol
  参考文献：
  名称：

  A concise synthesis of (±) and a total synthesis of (+)-epiquinamide

  摘要：

  A total synthesis of the quinolizidine alkaloid (+)-epiquinamide 1 has been achieved starting from (-)-pipecolinic acid 3. The key step is the highly diastereoselective addition of a TBDMS-protected propargyl alcohol to a chiral aldehyde derived from 3 to give erythro alkynol 19, which is then easily transformed into the desired bicyclic skeleton. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.05.092

文献信息

• An approach towards the total synthesis of (+)-epiquinamide and (+)-α-conhydrine from Garner aldehyde
  作者：Ajay Kumar Srivastava、Sanjit Kumar Das、Gautam Panda

  DOI：10.1016/j.tet.2009.04.074

  日期：2009.7

  A short and stereoselective route for the synthesis of 1-hydroxyquinolizidine, an advanced synthetic intermediate for the total synthesis of (+)-epiquinamide is presented. The key synthetic steps involve diastereoselective nucleophilic addition on l-serine derived Garner aldehyde and acid mediated (PTSA) ring closing metathesis. The methodology is also elaborated successfully for the total synthesis

  提出了一种短而立体的合成1-羟基喹oli嗪的立体选择途径，1-羟基喹oli嗪是一种用于（+）-表喹酰胺全合成的高级合成中间体。关键的合成步骤涉及在1-丝氨酸衍生的加纳醛上的非对映选择性亲核加成和酸介导的（PTSA）闭环复分解。该方法还成功地阐述了全合成重要的哌啶生物碱（+）-α-conhydrine的方法。
• A concise synthesis of (±) and a total synthesis of (+)-epiquinamide
  作者：Sok Teng (Amy) Tong、David Barker

  DOI：10.1016/j.tetlet.2006.05.092

  日期：2006.7

  A total synthesis of the quinolizidine alkaloid (+)-epiquinamide 1 has been achieved starting from (-)-pipecolinic acid 3. The key step is the highly diastereoselective addition of a TBDMS-protected propargyl alcohol to a chiral aldehyde derived from 3 to give erythro alkynol 19, which is then easily transformed into the desired bicyclic skeleton. (c) 2006 Elsevier Ltd. All rights reserved.